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Chemical Compound Review:

Bppp-cssaa (2S)-2-[[(2S)-3- aminocarbonyl-2-[[(2S)-2...

Synonyms: P3C-Ssna, AC1L37A2, 87173-03-3, Pam3Cys-ser-ser-asn-ala, Tripalmitoyl pentapeptide

Lex, A. et al., Hoffmann, P. et al., Biesert, L. et al., Scheuer, W.V. et al., Kleine, B. et al., et al.

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Disease relevance of Bppp-cssaa

A synthetic analogue of Escherichia coli lipoprotein, tripalmitoyl pentapeptide, constitutes a potent immune adjuvant [1].
Lipoprotein from the outer membrane of Escherichia coli and its synthetically prepared N-terminal lipopeptide segments Pam3Cys-Ser-Ser-Asn-Ala and Pam3Cys-Ser, as well as lipoprotein from other Enterobacteriaceae, constitute potent polyclonal B lymphocyte activators [2].
Vaccines consisting of acetone-killed Salmonella typhimurium were supplemented with a synthetically prepared lipopeptide derivative of bacterial lipoprotein, Pam3Cys-Ser-Ser-Asn-Ala [3].

High impact information on Bppp-cssaa

Addition of tripalmitoyl pentapeptide to the cell cultures 1 day after or 1 day before antigen application had no significant positive effect, and in several instances a decrease in antibody production was found [1].
It also exhibits a strong adjuvant activity in vitro: In the presence of 3.3 to 33.3 micrograms/ml of tripalmitoyl pentapeptide, the stimulation of the primary antibody response toward underivatized sheep red blood cells (SRBC) and toward trinitrophenylated (TNP-) SRBC was markedly enhanced, as measured by a direct hemolytic plaque assay [1].
Mitogenic activities of synthetic Escherichia coli lipid A and a synthetic partial structure (tripalmitoyl pentapeptide) of E. coli lipoprotein [4].
By analysing the frequencies of precursor cells reactive to TPP or LPS and the isotype patterns obtained after stimulation, we demonstrated that both mitogens activate individual B cells in different ways [5].
Proteins bound to the column were selectively eluted by a solution of tripalmitoyl pentapeptide, and the fractions were analyzed by sodium dodecyl sulphate/polyacrylamide gel electrophoresis and autoradiography [6].

Biological context of Bppp-cssaa

By affinity chromatography using an affinity adsorbent prepared by coupling the lipoprotein analogue to CPG-aminopropyl derivatized glass beads, we could enrich one major binding protein for tripalmitoyl-pentapeptide from mouse serum, which was identified as albumin [7].

Anatomical context of Bppp-cssaa

The mechanism of the binding of lipoprotein to lymphocytes was investigated by using the synthetic analogue of its N-terminal part, S-[2,3-bis(palmitoyloxy)-(2RS)-propyl]-N-palmitoyl-(R)-cysteinyl-( S)-seryl- (S)-seryl-(S)-asparaginyl-(S)-alanine (tripalmitoyl pentapeptide) [6].

Analytical, diagnostic and therapeutic context of Bppp-cssaa

In the presence of tripalmitoyl pentapeptide, the antigen-specific IgM response was increased about sevenfold and the IgG response was augmented about 10-fold, as measured by ELISA [1].

References

A synthetic analogue of Escherichia coli lipoprotein, tripalmitoyl pentapeptide, constitutes a potent immune adjuvant. Lex, A., Wiesmüller, K.H., Jung, G., Bessler, W.G. J. Immunol. (1986) [Pubmed]
Stimulation of human and murine adherent cells by bacterial lipoprotein and synthetic lipopeptide analogues. Hoffmann, P., Heinle, S., Schade, U.F., Loppnow, H., Ulmer, A.J., Flad, H.D., Jung, G., Bessler, W.G. Immunobiology (1988) [Pubmed]
Enhancement of protection against Salmonella infection in mice mediated by a synthetic lipopeptide analogue of bacterial lipoprotein in S. typhimurium vaccines. Schlecht, S., Wiesmüller, K.H., Jung, G., Bessler, W.G. Zentralbl. Bakteriol. (1989) [Pubmed]
Mitogenic activities of synthetic Escherichia coli lipid A and a synthetic partial structure (tripalmitoyl pentapeptide) of E. coli lipoprotein. Brade, L., Bessler, W.G., Brade, H. Infect. Immun. (1988) [Pubmed]
Polyclonal B-cell activation by a synthetic analogue of bacterial lipoprotein is functionally different from activation by bacterial lipopolysaccharide. Kleine, B., Sprenger, R., Martinez-Alonso, C., Bessler, W.G. Immunology (1987) [Pubmed]
Interaction of mitogenic bacterial lipoprotein and a synthetic analogue with mouse lymphocytes. Isolation and characterization of binding proteins. Biesert, L., Scheuer, W., Bessler, W.G. Eur. J. Biochem. (1987) [Pubmed]
Binding of a synthetic analogue of mitogenic bacterial lipoprotein to murine major histocompatibility complex (MHC) gene products. Scheuer, W.V., Biesert, L., Bessler, W.G. Biol. Chem. Hoppe-Seyler (1986) [Pubmed]

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